Basic Concepts of Organic

Chemistry

Hybridization
 Hybridization

“Hybridization is defined as the concept of mixing two

atomic orbital's with the same energy levels to give a
degenerated new type of orbital's.”

 This intermixing is based on quantum mechanics. The atomic

orbital's of the same energy level can only take part in
hybridization and both full filled and half-filled orbital's can
also take part in this process provided they have equal energy.

During the process of hybridization, the atomic orbital's of

similar energy are mixed together such as the mixing of two ‘s’
orbital's or two ‘p’ orbital’s or mixing of an ‘s’ orbital with a ‘p’
orbital or ‘s’ orbital with a ‘d’ orbital.
 What is Hybridization?

 Redistribution of the energy of orbital's of individual

atoms to give orbital's of equivalent energy happens
when two atomic orbital's combine together to form
hybrid orbital in a molecule. This process is called
hybridization. The new orbital's thus formed are
known as hybrid orbital's.

 Types of Hybridization:
 Based on the types of orbital's involved in mixing,
the hybridization can be classified as sp3, sp2, sp,
sp3d, sp3d2, sp3d3.
 Determining Hybridization is as easy
as counting electron domains
 The number of electron domains on an atom determines the
number of hybrid orbital's required and thus the hybridization.
 Misconception alert..
 Hybrid orbital's can be used for both bonding
and non-bonding electrons . This is why we
need to count the number of electron domains ,
not just the number if bonds.

 Recall that a double bond and triple bond only

count as a single domain .This does not change
for determining hybridization.
 Types of Hybridization
 Let us now discuss the various types of hybridization
along with their examples

1. sp3 Hybridization:
“When one ‘s’ orbital and 3 ‘p’ orbital's belonging to the
same shell of an atom mix together to form four new
equivalent orbital, the type of hybridization is called
a tetrahedral hybridization or sp3. The new orbital's
formed are called sp3 hybrid orbital's.”

• These are directed towards the four corners of a regular

tetrahedron and make an angle of 109°28’ with one another.
 Contd…
 The angle between the  Electronic Configuration
sp3 hybrid orbital's is of Carbon in Sp3
109.280 Hybridization:

 Each sp3 hybrid orbital

has 25% s character and
75% p character.
 Examples of sp3 Hybridization:

 ethane (C2H6), methane

 Summary
 Sp3 Hybridization occurs
when a carbon has four
attached groups
 Sp3 hybrid orbital has 25% s
and 75% p character.
 Each Sp3 hybrid orbital is
involved in a σ bond
formation.
 4 Sp3 hybrids point towards
the corner of a tetrahedron
at 109°28’ to each other.
Formation of σ bond:
 2. sp  Hybridization
2

“sp2 hybridization is observed when one s and

two p orbital's of the same shell of an atom mix
to form 3 equivalent orbital. The new orbital's
formed are called sp2 hybrid orbital's. ”

• sp2 hybridization is also called trigonal hybridization.

• It involves mixing of one ‘s’ orbital and two ‘p’
orbital’s of equal energy to give a new hybrid orbital
known as sp2.
 Contd…
 A mixture of s and p orbital
formed in trigonal symmetry and
is maintained at 1200.
 All the three hybrid orbital's
remain in one plane and make an
angle of 120° with one another.
Each of the hybrid orbital's
formed has 33.33% s character
and 66.66% ‘p’ character.
 The molecules in which the
central atom is linked to 3 atoms
and is sp2 hybridized have a
triangular planar shape.
 A double bond=σ + π bond
 Examples of sp2 Hybridization
 All the compounds  Bonding in Ethane:
of Boron i.e. BF3,
BH3

 All the
compounds of carb
on
containing a
carbon-carbon
double bond,
Ethylene (C2H4)
 Formation of π bond:
 Remaining p orbital's
from sp or sp2 form pi
bond.
 Pi bond is formed only
when sigma bond
already exist.
 Contd…
 Pi bond hinders free
rotation about the carbon
– to – carbon bond.
 Types of Hybridization
3. sp Hybridization:
“sp hybridization is observed when one s and one p
orbital in the same main shell of an atom mix to form
two new equivalent orbital's. The new orbital's formed
are called sp hybridized orbital's. It forms linear
molecules with an angle of 180°.”

This type of hybridization involves the mixing of one ‘s’ orbital

and one ‘p’ orbital of equal energy to give a new hybrid orbital
known as an sp hybridized orbital.
 Contd…
 sp hybridization is also called diagonal
hybridization.
 Each sp hybridized orbital has an equal amount
of s and p character, i.e., 50% s and p
character.
 Examples of sp Hybridization:
 All compounds of beryllium like BeF2, BeH2, BeCl2
 All compounds of carbon-containing triple Bond like
C2H2.
Bonding in Acetylene:
Bonding in Acetylene:
 Summary
 Sp hybridization occurs when a C has
2 attached groups.
 Sp hybrid orbital has 50% s and50%
p character.
 The two sp hybrids are oriented at an
angle of 180o to each other.
 Each sp hybrid orbital is involved in a
σ bond formation and the
remaining two p orbital's form two
π bonds.
 A triple bond= one σ+two π bonds
 4. sp d Hybridization
3

“sp3d hybridization involves the mixing of 3p

orbital's and 1d orbital to form 5 sp3d hybridized
orbital's of equal energy. They have trigonal
bipyramidal geometry.”

• The mixture of s, p and d orbital forms trigonal bipyramidal

symmetry.
• Three hybrid orbital's lie in the horizontal plane inclined at an
angle of 120° to each other known as the equatorial orbital's.
 Contd…
 The remaining two
orbital's lie in the vertical
plane at 90 degrees plane
of the equatorial orbital's
known as axial orbital's.
 Example:
Hybridization in Phosph
orus
pentachloride (PCl5)
 5. sp d Hybridization
3 2 

 sp3d2 hybridization has 1s, 3p and 2d orbital's, that

undergo intermixing to form 6 identical sp3d2
hybrid orbital's.

 These 6 orbital's are directed towards the corners of

an octahedron.

 They are inclined at an angle of 90 degrees to one

another.
 Example : sulfur hexafluoride
 Key Features of Hybridization
 Atomic orbital's with equal energies undergo
hybridization

 The number of hybrid orbital's formed is equal to

the number of atomic orbital's mixing.

 It is not necessary that all the half-filled orbital's

must participate in hybridization. Even completely
filled orbital's with slightly different energies can
also participate
.
 Contd…
 Hybridization happens only during the bond
formation and not in an isolated gaseous atom.

 The shape of the molecule can be predicted if

hybridization of the molecule is known.

 The bigger lobe of the hybrid orbital always

has a positive sign while the smaller lobe on
the opposite side has a negative sign.
 Five basic shapes of Hybridization
 The five basic shapes of hybridization are linear, trigonal planar, tetrahedral,
trigonal bipyramidal, and octahedral.

 The geometry of the orbital arrangement:

 Linear: Two electron groups involved resulting in sp hybridization, the angle

between the orbital's is 180°.
 Trigonal planar: Three electron groups involved resulting in sp2 hybridization,
the angle between the orbital's is 120°.
 Tetrahedral: Four electron groups involved resulting in sp3 hybridization, the
angle between the orbital's is 109.5°.
 Trigonal bipyramidal: Five electron groups involved resulting in sp3d
hybridization, the angle between the orbital's is 90°, 120°.
 Octahedral: Six electron groups involved resulting in sp3d2 hybridization, the
angle between the orbital's is 90°
 Amide molecule looks sp3 hybridized but
it is sp2, why?

 The general process of hybridization will

change if the atom is either enclosed by two or
more p orbital's or it has a lone pair to jump
into a p orbital. Therefore, in the case of amide
molecule, the lone pair goes into a p orbital to
have 3 adjacent parallel p orbital's
(conjugation).
 Why the hybrid orbital during
hybridization is better than their
parent atoms?

 The reason why a hybrid orbital is better than

their parents:

 Parent s: because it is directional unlike the s

orbital.
 Parent p: because it has lower energy than p
orbital
Pause and Practice
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